What is the most punctual flight time for Orlando to Chicago flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

What airlines fly to Chicago?

Frontier, American Airlines and Spirit Airlines are the top three most popular airlines that fly to Chicago from Orlando according to our data. Frontier is the first choice among our users, with 37% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Which airline has the best punctuality record on Orlando to Chicago flights?

According to our data, Denver Air Connection have had the least number of delays on this route over the last 12 months; with no flights being classified as delayed.

What is the cheapest airline that flies from Orlando to Chicago?

Allegiant Air, Spirit Airlines, and Frontier are the most popular carriers operating from Orlando to Chicago

How often are flights from Orlando to Chicago delayed?

Historically, on average around 15% of flights between Orlando and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 155 minutes.

What day of the week experiences the fewest flight delays on this route?

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Saturday has historically seen more delays on average compared to the rest of the week.

How many flights depart from Orlando to Chicago on average per week?

As of November 2025, 283 flights take off from Orlando and land in Chicago each week. The most common flight departure day for this route is Thu, with 23% of weekly flights taking off on this day.

How many flights depart from Orlando to Chicago on average per day?

As of November 2025, there are 40 flights per day flying from Orlando to Chicago. The most common time of day flights depart is 6:00PM, with 41% of flights taking off in the afternoon.

When did momondo last update prices for flights from Orlando to Chicago?

Prices for flights from Orlando to Chicago refresh daily.

How many operators does momondo search for flights from Orlando to Chicago?

The number of operators available for flights from Orlando to Chicago is 7 as of November 2025.

How old do you have to be to fly from Orlando to Chicago?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Orlando to Chicago.

What documentation or ID do you need to fly to Chicago?

The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$49 Cheap Flights from Orlando to Chicago in 2025/26

Q: What is the typical price of a round-trip flight between Orlando and Chicago?

Prices are currently low for flights on this route. Typical prices usually range from $134 to $287. The lowest price recently found on this route was $73.

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Cheap round-trip flights

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7:58 pm - 9:58 pmMCO-MDW

3h 00mnonstop

3:10 pm - 6:58 pmMDW-MCO

2h 48mnonstop

$73Frontier

Find Deal

Thu, Dec 11 - Mon, Dec 15

7:58 pm - 9:58 pmMCO-MDW

3h 00mnonstop

3:10 pm - 6:58 pmMDW-MCO

2h 48mnonstop

$74Frontier

Find Deal

Thu, Dec 11 - Mon, Dec 15

11:00 am - 12:48 pmSFB-RFD

2h 48mnonstop

1:38 pm - 5:15 pmRFD-SFB

2h 37mnonstop

$75Allegiant Air

Find Deal

Sat, Dec 6 - Sat, Dec 13

8:40 pm - 10:39 pmMCO-MDW

2h 59mnonstop

6:37 pm - 10:23 pmMDW-MCO

2h 46mnonstop

$75Frontier

Find Deal

Fri, Dec 12 - Sun, Dec 14

11:00 am - 1:16 pmMCO-ORD

3h 16mnonstop

2:26 pm - 6:31 pmORD-MCO

3h 05mnonstop

$76Frontier

Find Deal

Sat, Dec 13 - Mon, Dec 15

11:00 am - 1:16 pmMCO-ORD

3h 16mnonstop

7:20 am - 11:12 amORD-MCO

2h 52mnonstop

$79Multiple Airlines

Find Deal

Sat, Dec 13 - Sun, Dec 14

7:58 pm - 9:58 pmMCO-MDW

3h 00mnonstop

3:10 pm - 6:58 pmMDW-MCO

2h 48mnonstop

$79Frontier

Find Deal

Thu, Dec 25 - Wed, Dec 31

11:00 am - 1:16 pmMCO-ORD

3h 16mnonstop

7:20 am - 11:12 amORD-MCO

2h 52mnonstop

$80Multiple Airlines

Find Deal

Sat, Dec 6 - Sun, Dec 14

11:00 am - 12:48 pmSFB-RFD

2h 48mnonstop

1:38 pm - 5:15 pmRFD-SFB

2h 37mnonstop

$82Allegiant Air

Find Deal

Sat, Dec 6 - Sat, Dec 13

12:17 pm - 2:21 pmMCO-ORD

3h 04mnonstop

7:20 am - 11:12 amORD-MCO

2h 52mnonstop

$84Spirit Airlines

Find Deal

Thu, Dec 11 - Sun, Dec 14

Spirit Airlines flights from Orlando to Chicago

Our best Spirit Airlines deals on Orlando to Chicago flight tickets

Spirit Airlines

Dec 11

MCO12:17 pmOrlando

3h 04m

ORD2:21 pmChicago O'Hare Intl

Dec 15

ORD12:09 pmChicago O'Hare Intl

2h 52m

MCO4:01 pmOrlando

$84

Find similar

Spirit Airlines

Nov 22

MCO9:00 pmOrlando

3h 06m

ORD11:06 pmChicago O'Hare Intl

Dec 8

ORD7:20 amChicago O'Hare Intl

2h 52m

MCO11:12 amOrlando

$88

Find similar

Spirit Airlines

Dec 5

MCO7:44 pmOrlando

3h 04m

ORD9:48 pmChicago O'Hare Intl

Dec 8

ORD7:20 amChicago O'Hare Intl

2h 52m

MCO11:12 amOrlando

$97

Find similar

Frontier flights from Orlando to Chicago

Our best Frontier deals on Orlando to Chicago flight tickets

Frontier

Dec 11

MCO7:58 pmOrlando

3h 00m

MDW9:58 pmChicago Midway

Dec 15

MDW3:10 pmChicago Midway

2h 48m

MCO6:58 pmOrlando

$73

Find similar

Frontier

Dec 11

MCO7:58 pmOrlando

3h 00m

MDW9:58 pmChicago Midway

Dec 15

MDW3:10 pmChicago Midway

2h 48m

MCO6:58 pmOrlando

$74

Find similar

Frontier

Dec 12

MCO8:40 pmOrlando

2h 59m

MDW10:39 pmChicago Midway

Dec 14

MDW6:37 pmChicago Midway

2h 46m

MCO10:23 pmOrlando

$75

Find similar

Fly from

Fly to

Route

Depart

Return

Price

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 12/11

7:58 pm-9:58 pm

Nonstop3h 00m

Chicago Midway

Mon 12/15

3:10 pm-6:58 pm

Nonstop2h 48m

$73

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 12/11

7:58 pm-9:58 pm

Nonstop3h 00m

Chicago Midway

Mon 12/15

3:10 pm-6:58 pm

Nonstop2h 48m

$74

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Sat 12/6

11:00 am-12:48 pm

Nonstop2h 48m

Chicago Greater Rockford

Sat 12/13

1:38 pm-5:15 pm

Nonstop2h 37m

$75

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 12/12

8:40 pm-10:39 pm

Nonstop2h 59m

Chicago Midway

Sun 12/14

6:37 pm-10:23 pm

Nonstop2h 46m

$75

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 12/13

11:00 am-1:16 pm

Nonstop3h 16m

Chicago O'Hare Intl

Mon 12/15

2:26 pm-6:31 pm

Nonstop3h 05m

$76

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 12/13

11:00 am-1:16 pm

Nonstop3h 16m

Chicago O'Hare Intl

Sun 12/14

7:20 am-11:12 am

Nonstop2h 52m

$79

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 12/25

7:58 pm-9:58 pm

Nonstop3h 00m

Chicago Midway

Wed 12/31

3:10 pm-6:58 pm

Nonstop2h 48m

$79

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 12/6

11:00 am-1:16 pm

Nonstop3h 16m

Chicago O'Hare Intl

Sun 12/14

7:20 am-11:12 am

Nonstop2h 52m

$80

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Sat 12/6

11:00 am-12:48 pm

Nonstop2h 48m

Chicago Greater Rockford

Sat 12/13

1:38 pm-5:15 pm

Nonstop2h 37m

$82

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 12/11

12:17 pm-2:21 pm

Nonstop3h 04m

Chicago O'Hare Intl

Sun 12/14

7:20 am-11:12 am

Nonstop2h 52m

$84

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Orlando to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Delays

Other information

What is the typical price of a round-trip flight between Orlando and Chicago?

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Orlando, with most prices found around $117. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from Orlando to Chicago during January average around $149.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $236. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Orlando to Chicago for around $451.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Orlando to Chicago during this time can be as low as $237. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $517.

What is the cheapest Orlando to Chicago flight route?

Fly from Orlando to Chicago Midway for the best Orlando - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Orlando when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $214 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Orlando for as low as $176 on momondo.

What cabin class options are available on Orlando to Chicago flights?

There are 4 cabin classes available to choose from on Orlando to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Orlando to Chicago flights?

No. A direct flight is the cheapest option for a flight between Orlando to Chicago.

How have Orlando to Chicago flight prices changed over time?

As of November 2025, prices for Orlando to Chicago flights are approximately 10% cheaper when compared to flights at the same time last year.

When to book flights from Orlando to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Orlando to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Orlando to Chicago (ORL to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Orlando to Chicago

Best Price Found	$56
Fastest flight time	2h 46m
Direct flights	Mon, Tue, Wed, Thu, Sat and Sun
Airports in Chicago	2 airports

The best one-way flight to Chicago from Orlando in the past 72 hours is $56. The best round-trip flight deal from Orlando to Chicago found on momondo in the last 72 hours is $96.

The fastest flight from Orlando to Chicago takes 2h 46m

Direct flights go from Orlando to Chicago on Monday, Tuesday, Wednesday, Thursday, Saturday and Sunday. Airlines offering direct flights are: Allegiant Air and Frontier.

There are 2 airports near Chicago: Chicago Greater Rockford (RFD), Chicago Midway (MDW)

Search flight deals

How far is Orlando to Chicago by plane?
Chicago is 985.3 mi away from Orlando. 2h 48m is a normal flight duration for this route.
When did momondo last update prices for flights from Orlando to Chicago?
Prices for flights from Orlando to Chicago refresh daily.
How many operators does momondo search for flights from Orlando to Chicago?
The number of operators available for flights from Orlando to Chicago is 7 as of November 2025.
How old do you have to be to fly from Orlando to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Orlando to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Orlando to Chicago?
Based on momondo bookings for flights between Orlando and Chicago, the leading plane model is Airbus A321neo, making up 18.59% of the total bookings. Other popular models include Airbus A320neo with 10.52%, Airbus A321 (sharklets) with 10.25%, and Boeing 737-800 with 10.01%.
What is the most popular airline from Orlando to Chicago?
momondo data reveals that the most frequently booked airline on the route from Orlando to Chicago is Frontier, representing 50% of all bookings. The subsequent popular airlines are Spirit Airlines at 18%, American Airlines at 15%, and Southwest at 11%.

Best airlines flying from Orlando to Chicago

Compare and see reviews for airlines that fly from Orlando to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $68	Free Cancellation	Rating 5.8 3,104 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $74	Free Cancellation	Rating 6.3 8,156 reviews	Search Spirit Airlines flights
Allegiant Air	PriceFrom $82	Free Cancellation	Rating 7.2 700 reviews	Search Allegiant Air flights
Delta	PriceFrom $114	Free Cancellation	Rating 7.9 8,002 reviews	Search Delta flights
United Airlines	PriceFrom $157	Free Cancellation	Rating 7.4 9,027 reviews	Search United Airlines flights
American Airlines	PriceFrom $158	Free Cancellation	Rating 7.2 11,045 reviews	Search American Airlines flights
Southwest	PriceFrom $159	Free Cancellation	Rating 8.0 4,249 reviews	Search Southwest flights

Southwest Flights From Orlando to Chicago
Southwest is one of the most popular airlines flying from Orlando to Chicago, operating 18 flights/week on average for this route. A good Southwest flight deal for Orlando to Chicago starts from $159 round-trip, up to an average price of $292. Our users have rated Southwest at 8.0/10.
United Airlines Flights From Orlando to Chicago
$157 is the best United Airlines flight deal from Orlando to Chicago found on momondo over the last 72 hours. The average United Airlines ticket price found was closer to $316, however, with flight time and availability significantly affecting the price. United Airlines (7.4/10 from 9,027 user reviews) flies into Chicago from Orlando 37 times in an average week so prices can vary.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Orlando to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Orlando to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Orlando to Chicago with flexible booking policies on momondo?

Flights from Orlando to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Orlando to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Orlando.

I’m not ready to book a flight from Orlando to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Orlando are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

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Flights to New Yorkfrom $44

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Flights to Orlandofrom $39

Flights to Las Vegasfrom $49

Flights to San Franciscofrom $55

Flights to Washington, D.C.from $36

Flights to Bostonfrom $58

Flights to Atlantafrom $38

Flights to Dallasfrom $45

Flights to Seattlefrom $57

Flights to Denverfrom $48

Cheap flights from Orlando to Chicago from $49

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Orlando to Chicago departing on 12/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Our best Spirit Airlines deals on Orlando to Chicago flight tickets

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How to get the cheapest flight ticket from Orlando to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Orlando and Chicago?

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Orlando, with most prices found around $117. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from Orlando to Chicago during January average around $149.

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Orlando to Chicago during this time can be as low as $237. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $517.

What is the cheapest Orlando to Chicago flight route?

Fly from Orlando to Chicago Midway for the best Orlando - Chicago flight prices

How far in advance should I book a flight to Chicago?

What cabin class options are available on Orlando to Chicago flights?

There are 4 cabin classes available to choose from on Orlando to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Orlando to Chicago flights?

No. A direct flight is the cheapest option for a flight between Orlando to Chicago.

How have Orlando to Chicago flight prices changed over time?

As of November 2025, prices for Orlando to Chicago flights are approximately 10% cheaper when compared to flights at the same time last year.

What is the cheapest airline that flies from Orlando to Chicago?

Allegiant Air, Spirit Airlines, and Frontier are the most popular carriers operating from Orlando to Chicago

What airlines fly to Chicago?

How often are flights from Orlando to Chicago delayed?

Historically, on average around 15% of flights between Orlando and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 155 minutes.

What is the most punctual flight time for Orlando to Chicago flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Saturday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on Orlando to Chicago flights?

According to our data, Denver Air Connection have had the least number of delays on this route over the last 12 months; with no flights being classified as delayed.

How many flights depart from Orlando to Chicago on average per day?

As of November 2025, there are 40 flights per day flying from Orlando to Chicago. The most common time of day flights depart is 6:00PM, with 41% of flights taking off in the afternoon.

How many flights depart from Orlando to Chicago on average per week?

As of November 2025, 283 flights take off from Orlando and land in Chicago each week. The most common flight departure day for this route is Thu, with 23% of weekly flights taking off on this day.

When to book flights from Orlando to Chicago

Cheap Orlando to Chicago (ORL to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Orlando to Chicago

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

How far is Orlando to Chicago by plane?

When did momondo last update prices for flights from Orlando to Chicago?

How many operators does momondo search for flights from Orlando to Chicago?

How old do you have to be to fly from Orlando to Chicago?

What documentation or ID do you need to fly to Chicago?

What is the most popular plane model from Orlando to Chicago?

What is the most popular airline from Orlando to Chicago?

Best airlines flying from Orlando to Chicago

Compare and see reviews for airlines that fly from Orlando to Chicago with momondo

Southwest Flights From Orlando to Chicago

United Airlines Flights From Orlando to Chicago

Traveling to a place near Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from Orlando to Chicago?

Can I find flights from Orlando to Chicago with flexible booking policies on momondo?

How can momondo help me find flights from Orlando to Chicago?

I’m not ready to book a flight from Orlando to Chicago right now. Can momondo alert me if prices change?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.